239097-74-6,A common heterocyclic compound, 239097-74-6,Benzo[d]isoxazol-5-amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a suspension of intermediate ester (105 mg, 0.340 mmol) in DMF (0.5 mL) was added a solution of 1,2-benoxazol-5-amine (46 mg, 0.340 mmol) in DMF (0.5 mL). The reaction mixture was stirred at room temperature for 2 hours until the reaction was complete, and quenched with the addition of TFA (5 drops). The precipitated solid was collected by filtration, suspended in DCM, basified with saturated NaHCO3 to pH ~8. The aqueous layer was extracted with DCM, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by trituration in DCM/Et2O, collected by filtration, and dried in vacuo to give the title compound (50 mg, 48%) as a yellow solid.1H NMR (400 MHz, CDCl3): delta 10.05 (s, 1H), 8.72 (s, 1H), 8.55 (s, 1H), 8.07 (s, 1H), 7.68 (dd, J = 6.8 Hz, 1.6 Hz, 1H), 7.59 (d, J = 6.8 Hz, 1H), 6.59 (s, 1H), 2.71 (s, 3H), 2.70 (s, 3H). LC-MS m/z: 308.1 [M+H+]. HPLC Purity (214 nm): 98%; tR = 8.38 min.
The chemical industry reduces the impact on the environment during synthesis, 239097-74-6,Benzo[d]isoxazol-5-amine,I believe this compound will play a more active role in future production and life.
Reference£º
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse Marie, Josee; (134 pag.)WO2016/73889; (2016); A1;,
Benzisoxazole – Wikipedia
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